3α,7α,12α-trihydroxy-5β-cholane-24-carboxylic acid methyl ester | 59445-12-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 英文名称: 3α,7α,12α-trihydroxy-5β-cholane-24-carboxylic acid methyl ester
• 英文别名: 3α,7α,12α-Trihydroxy-5β-cholan-24-carbonsaeure-methylester；3α,7α,12α-Trihydroxy-26.27-dinor-5β-cholestansaeure-(25)-methylester；methyl (5R)-5-[(3R,5S,7R,8R,9S,10S,12S,13R,14S,17R)-3,7,12-trihydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]hexanoate
• CAS: 59445-12-4
• 化学式: C₂₆H₄₄O₅
• 分子量: 436.632
• InChiKey: LEHTYSFVJCGXTB-HZAMXZRMSA-N

物化性质

• 熔点：
  166-168 °C
• 沸点：
  552.5±50.0 °C(Predicted)
• 密度：
  1.129±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  31
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.96
• 拓扑面积：
  87
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3α,7α,12α-trihydroxy-5β-cholane-24-carboxylic acid methyl ester 在 silver carbonate 作用下， 以 甲苯 为溶剂， 反应 4.0h， 生成 7α,12α,25-trihydroxy-5β-cholestan-3-one
  参考文献：
  名称：

  Bile acids. LXXIII. Synthesis of analogs of 7α-hydroxy-4-cholesten-3-one as substrates for hepatic steroid 12α-hydroxylase

  摘要：

  Analogs of 7 alpha-hydroxy-4-cholesten-3-one were prepared to ascertain structural features necessary for maximal activity of hepatic microsomal 12 alpha-steroid hydroxylase. Methyl 3 alpha,7 alpha-dihydroxy-5 beta-cholane-24-carboxylate derived from chenodeoxycholic acid was oxidized at C-3 with silver carbonate/Celite. The product was hydrolyzed and dehydrogenated with SeO2 to provide 3-oxo-7 alpha-hydroxy-4-cholene-24-carboxylic acid. 5 beta-Cholestane-3 alpha,7 alpha,25-triol and 5 beta-cholestane-3 alpha,7 alpha,12 alpha,25-tetrol were similarly oxidized at C-3 and dehydrogenated to provide 7 alpha,25-dihydroxy-4-cholesten-3-one and 7 alpha,12 alpha,25-trihydroxy-4-cholesten-3-one, respectively. The products were characterized by thin-layer and gas chromatography, ultraviolet, infrared, proton resonance and mass spectrometry.

  DOI：

  10.1016/s0039-128x(84)80020-3
• 作为产物：
  描述：

  cholic acid triformate 在 草酰氯 、 甲烷磺酸 、 silver nitrate 作用下， 以 甲醇 为溶剂， 反应 6.01h， 生成 3α,7α,12α-trihydroxy-5β-cholane-24-carboxylic acid methyl ester
  参考文献：
  名称：

  7β-hydroxy bile alcohols: Facile synthesis and 2D 1H NMR studies of 5β-cholestane-3α,7β,12α,25-tetrol

  摘要：

  A rapid and easily performed procedure for the synthesis of 5 beta-cholestane-3 alpha, 7 beta, 12 alpha, 25-tetrol by means of an efficient homologation sequence of the intermediate, 3 alpha, 7 beta, 12 alpha-triformyloxy-24-oxo-25-diazo-25-homo-5 beta-cholane is described. The reaction sequence involved treating the intermediate, alpha-diazoketone in methanol with 3% AgNO3 or Ag2O, anhydrous Na2CO3, Na2S2O3/H2O resulting in the formation of homoursocholic acid in high yield. Esterification of the homoursocholic acid in methanol containing a catalytic amount of methanesulfonic acid under microwave irradiation conditions gave methyl homoursocholate. The subsequent treatment of methyl homoursocholate with methyl magnesium iodide provided 5 beta-cholestane-3 alpha,7 beta,12 alpha,25-tetrol in 88% yield The products and synthetic intermediates prepared in these studies were fully characterized by the results of 1D and 2D NMR, and high-resolution mass spectral studies. These studies will help in further investigation of the defect of cholic acid biosynthesis in patients with cerebrotendinous xanthomatosis (CTX) as well as other inborn errors of bile acid metabolism. (C) 1997 by Elsevier Science Inc.

  DOI：

  10.1016/s0039-128x(97)00007-x

文献信息

• A pentacarbomethoxycyclopentadiene (PCCP) organic Brønsted acid catalyzed stereoselective glycosidation of N-pentenyl orthoesters (NPOE) of d-glucose and d-galactose, in conjunction with N-iodosuccinimide
  作者：Maniyamma Aswathy、Balan Abhijith、Ravi S. Lankalapalli、Kokkuvayil V. Radhakrishnan

  DOI：10.1016/j.carres.2022.108684

  日期：2022.12

  we report our preliminary results in utilizing the organic Brønsted acid, pentacarbomethoxycyclopentadiene (PCCP), for catalysing the glycosidation with n-pentenyl orthoesters (NPOE) of d-glucose and d-galactose in the presence of N-iodosuccinimide (NIS). Benzoyl and benzyl protection in d-glucosyl NPOEs led to 1,2-trans glycosides, while acetyl protection in NPOE led to a mixture of 1,2-cis and trans

  在此，我们报告了在 N-碘代琥珀酰亚胺 (NIS) 存在下，利用有机布朗斯台德酸五甲氧基环戊二烯 (PCCP) 催化d -葡萄糖和d -半乳糖的正戊烯基原酸酯 (NPOE)糖苷化的初步结果。d-葡萄糖基 NPOE中的苯甲酰基和苄基保护导致 1,2-反式糖苷，而 NPOE 中的乙酰基保护导致 1,2-顺式和反式糖苷的混合物，顺式选择性 >75%，并且d-半乳糖基 NPOE 导致 1,2-原酸酯。底物范围与天然产物相关性的受体一起得到证明。本文重点介绍了利用有机布朗斯台德酸 PCCP 进行立体选择性糖苷化的前景。
• The Preparation of C-27 Steroids from Bile Acids. I. Coprostanetetrol-3(α), 7(α),12(α),25
  作者：W. H. Pearlman

  DOI：10.1021/ja01198a066

  日期：1947.6
• KIHIRA, KENJI;KOSAKA, DAISAKU;UNE, MIZUHO;HIRAOKA, TOSHIHITO;KAJIYAMA, GO+, J. LABELL. COMPOUNDS AND RADIOPHARM., 24,(1987) N 12, 1421-1428
  作者：KIHIRA, KENJI、KOSAKA, DAISAKU、UNE, MIZUHO、HIRAOKA, TOSHIHITO、KAJIYAMA, GO+

  DOI：——

  日期：——